Before you breakout the holiday lights this year consider doing the following items to help prep the property for winter.
1. Blow off roofs and gutters to keep them clear of debris that can clog downspouts during storms. While you are up there I would recommend taking a closer look to make sure everything is in proper working order. Things to look for include; rusted gutters, worn or torn shingles and nail heads sticking up from the shingles. (All of which can be caught early and addressed by a local contractor or handy-person)
2. Pressure washing the house and gutters keep your house looking fresh and clean. This also lets you see what type of condition your paint and caulking are in. If you find sections that are starting to peel then this would be the time to address those issues before they become bigger problem. Dry-rot is the most common issue on siding that can be addressed if caught early. Dry-rot is caused when moisture penetrates wood surfaces that have paint peeling or lack proper caulking to seal the joints. (painting contractor or handy-person should be able to address these types of fixes)
3. Downspout drainage is a common issue in the Bay Area. Downspouts require the right ground slope or drainage to keep water from settling near the foundation. Check to make sure the areas around each downspout slope away from the foundation in order to prevent settling or excessive moisture from building up.
These are just a few things you can do to help extend the life of your home. Preventive maintenance is always less expensive than having to tackle a major remodel on something could have been addressed early on.